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Failed to connect to Let’s Encrypt. Please make sure your Diskstation and Router have Port 80…

I recently was annoyed by a strange error.

“Failed to connect to Let’s Encrypt. Please make sure your Diskstation and router have port 80 open to Let’s Encrypt domain validation from the Internet. All other communications with Let’s Encrypt go over HTTPS to keep your Diskstation secure.”

Is was searching for port forwarding issues on port 80 and 443. But seems all correct and working. Must be something else. Finally found the root cause.

The website was reachable using www sub- domain prefix but not without. Using mathiasirmer.com there was a not working redirection. As soon as I fixed this I was able to get the certificate from Lets Encrypt. So don’t let this error message guide you in the wrong way.

7 thoughts on “Failed to connect to Let’s Encrypt. Please make sure your Diskstation and Router have Port 80…”

I’m getting the same message, but I don’t have the same problem…I don’t think. I have a http://www.mydomain.com hosted by Blogger, so I can’t do a redirect. I’m trying to use a subdomain.mydomain.com for the Synology but am getting the same error.

My issue is that you can’t use an ASUS RT-68U to host Port 80 websites. It is an issue with the stock and Merlin firmware. There’s no way to fix it other than to swap routers out. That’s my next plan.